86044-00-0

Upstream product

• 71663-75-7 N-(benzyloxy)-3,3-dimethyl-2-azetidinone 
• 87070-48-2 N-(phenylmethoxy)-3-bromo-2,2-dimethyl-1-propanamine 
• 86043-99-4 N-(phenylmethoxy)-2,2-dimethyl-3-<<(4-methylphenyl)sulfonyl>oxy>-1-propanamine 
• 34795-31-8 3-bromo-2,2-dimethylpropionaldehyde 
• 21651-04-7 3-hydroxy-2,2-dimethylpropyl 4-methylbenzenesulfonate 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 622-33-3 N-benzyloxyamine 
• 86043-98-3 Toluene-4-sulfonic acid 3-benzyloxyimino-2,2-dimethyl-propyl ester 
• 87070-47-1 3-bromo-2,2-dimethyl-1-propanone O-(phenylmethyl)oxime 
• 18516-19-3 2,2-dimethyl-3-oxopropyl 4-methylbenzenesulfonate 
• 40894-00-6 3-bromo-2,2-dimethyl-propan-1-ol 

Relevant academic research and scientific papers

ACETOXYLATION OF 1-BENZYLOXY β-LACTAMS AT C-4 VIA A REDUCTION-OXIDATION SEQUENCE

Selective dihydroalane reduction of 1-benzyloxy β-lactams 4 affords 1-(benzyloxy)azetidines 6 which can be debenzylated to give the 1-hydroxy azetidines 7.Oxidation of the compounds 7 either gives a mixture of β-lactams 10 and 11 or selectively β-lactams

SYNTHESIS OF 1-HYDROXYAZETIDINES AND THEIR CONVERSION INTO 1,4-DIACETOXY-2-AZETIDINONES

1-Hydroxyazetidines (5), prepared by reductive cyclization of O-benzyl-β-tosyloxy oximes 1 and subsequent debenzylation, can be oxidized selectively either to four-membered cyclic nitrones (6 and 7) or to 1,4-diacetoxy-2-azetidinones (9).

Chemistry of Four-Membered Cyclic Nitrones. 5. Synthesis and Oxidation of 1-Hydroxyazetidines

1-(Benzyloxy)azetidines 9 are prepared by reductive cyclization of the corresponding O-benzyl oximes (6) that have a leaving group at the β-position.Reduction of the unprotected oxime 6a with sodium cyanoborohydride in acetic acid affords 3,4,4-trimethyli